Studies using radioisotopes. IV. The acid-catalysed rearrangement of 4-Hydroxy-3-nitroso-2-quinolones

Abstract

4-Hydroxy-3-nitroso-2-quinolone and its N-methyl derivative have been labelled with 14C at C2, C3, and C4, and the acid-catalysed rearrangement to isatin and isatoxime studied. Carbon dioxide arises from C2, and the trace of carbon monoxide from C4. Possible reaction pathways are discussed, and evidence is presented that dioxindole is implicated as an intermediate.